DE2736502C2 - Aromatische Dicarbonsäureester und ihre Verwendung in Flüssigkristallmaterialien für elektrooptische Anzeigevorrichtungen - Google Patents
Aromatische Dicarbonsäureester und ihre Verwendung in Flüssigkristallmaterialien für elektrooptische AnzeigevorrichtungenInfo
- Publication number
- DE2736502C2 DE2736502C2 DE2736502A DE2736502A DE2736502C2 DE 2736502 C2 DE2736502 C2 DE 2736502C2 DE 2736502 A DE2736502 A DE 2736502A DE 2736502 A DE2736502 A DE 2736502A DE 2736502 C2 DE2736502 C2 DE 2736502C2
- Authority
- DE
- Germany
- Prior art keywords
- dicarboxylic acid
- liquid crystal
- aromatic dicarboxylic
- acid esters
- udf54
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- -1 Aromatic dicarboxylic acid esters Chemical class 0.000 title claims description 23
- 239000004973 liquid crystal related substance Substances 0.000 title claims description 18
- 239000000463 material Substances 0.000 title claims description 17
- 239000000203 mixture Substances 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 14
- 239000012071 phase Substances 0.000 description 13
- 230000008859 change Effects 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- 210000004027 cell Anatomy 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 150000001991 dicarboxylic acids Chemical class 0.000 description 6
- 230000005684 electric field Effects 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- WIPYZRZPNMUSER-UHFFFAOYSA-N 2-chloro-4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1Cl WIPYZRZPNMUSER-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 230000007704 transition Effects 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 238000005863 Friedel-Crafts acylation reaction Methods 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 3
- 239000001110 calcium chloride Substances 0.000 description 3
- 229910001628 calcium chloride Inorganic materials 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- HORTUSNFKSBVHC-UHFFFAOYSA-N (4-pentylphenyl) 2-chloro-4-hydroxybenzoate Chemical compound C1=CC(CCCCC)=CC=C1OC(=O)C1=CC=C(O)C=C1Cl HORTUSNFKSBVHC-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000004990 Smectic liquid crystal Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 229950011260 betanaphthol Drugs 0.000 description 2
- OQNGCCWBHLEQFN-UHFFFAOYSA-N chloroform;hexane Chemical compound ClC(Cl)Cl.CCCCCC OQNGCCWBHLEQFN-UHFFFAOYSA-N 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- JGJLWPGRMCADHB-UHFFFAOYSA-N hypobromite Chemical compound Br[O-] JGJLWPGRMCADHB-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- LUZDYPLAQQGJEA-UHFFFAOYSA-N 2-Methoxynaphthalene Chemical compound C1=CC=CC2=CC(OC)=CC=C21 LUZDYPLAQQGJEA-UHFFFAOYSA-N 0.000 description 1
- 150000004786 2-naphthols Chemical class 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- XLMUTJIBIFYYNN-UHFFFAOYSA-N 4-[5-(4-butylphenyl)-1,3,2-dioxaborinan-2-yl]benzonitrile Chemical compound C1=CC(CCCC)=CC=C1C1COB(C=2C=CC(=CC=2)C#N)OC1 XLMUTJIBIFYYNN-UHFFFAOYSA-N 0.000 description 1
- ZNPSUQQXTRRSBM-UHFFFAOYSA-N 4-n-Pentylphenol Chemical compound CCCCCC1=CC=C(O)C=C1 ZNPSUQQXTRRSBM-UHFFFAOYSA-N 0.000 description 1
- VKNDODSBNIPGNL-UHFFFAOYSA-N 6-pentylnaphthalene-2-carboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(CCCCC)=CC=C21 VKNDODSBNIPGNL-UHFFFAOYSA-N 0.000 description 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 159000000032 aromatic acids Chemical class 0.000 description 1
- 125000005002 aryl methyl group Chemical group 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003098 cholesteric effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 210000002858 crystal cell Anatomy 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000374 eutectic mixture Substances 0.000 description 1
- 230000005496 eutectics Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000005911 haloform reaction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- CRWJEUDFKNYSBX-UHFFFAOYSA-N sodium;hypobromite Chemical compound [Na+].Br[O-] CRWJEUDFKNYSBX-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/32—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems
- C09K19/322—Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/202—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring the aromatic ring being a naphthalene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/29—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with halogen-containing compounds which may be formed in situ
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Crystallography & Structural Chemistry (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB33861/76A GB1587819A (en) | 1976-08-13 | 1976-08-13 | Aromatic diester liquid crystal materials |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2736502A1 DE2736502A1 (de) | 1978-02-16 |
| DE2736502C2 true DE2736502C2 (de) | 1987-04-02 |
Family
ID=10358402
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2736502A Expired DE2736502C2 (de) | 1976-08-13 | 1977-08-12 | Aromatische Dicarbonsäureester und ihre Verwendung in Flüssigkristallmaterialien für elektrooptische Anzeigevorrichtungen |
Country Status (14)
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1576106A (en) * | 1976-11-25 | 1980-10-01 | Secr Defence | Temperature compensated liquid crystal devices |
| NL169647B (nl) * | 1977-10-27 | 1982-03-01 | Philips Nv | Weergeefinrichting met een vloeibaar kristal. |
| GB2009219B (en) * | 1977-11-02 | 1982-04-28 | Secr Defence | Liquid ctystal material mixtures and devices incorporating such mixtures |
| US4291948A (en) * | 1977-11-10 | 1981-09-29 | International Standard Electric Corporation | Liquid crystal display incorporating positive and negative smectic material |
| GB2010560A (en) * | 1977-11-22 | 1979-06-27 | Suwa Seikosha Kk | Liquid crystal display arrangements |
| US4261652A (en) * | 1978-08-04 | 1981-04-14 | The Secretary Of State For Defence In Her Britannic Majesty's Government Of The United Kingdom Of Great Britain And Northern Ireland | Liquid crystal compounds and materials and devices containing them |
| DE2949080A1 (de) * | 1979-12-06 | 1981-06-11 | Merck Patent Gmbh, 6100 Darmstadt | Naphthalinderivate, diese enthaltende dielektrika und elektrooptisches anzeigeelement |
| EP0047817A3 (de) * | 1980-08-14 | 1982-05-26 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | Hydrierte Naphthaline, deren Herstellung und Verwendung sowie derartige Naphthaline enthaltende Gemische |
| DD160394A3 (de) * | 1980-09-29 | 1983-07-27 | Dietrich Demus | Anwendung fluessig-kristalliner substanzen |
| DE3131593A1 (de) | 1980-09-29 | 1982-06-24 | VEB Werk für Fernsehelektronik im VEB Kombinat Mikroelektronik, DDR 1160 Berlin | Kristallin-fluessige substanzen |
| GB2085910B (en) * | 1980-10-13 | 1985-05-22 | Secr Defence | A liquid crystal composition comprising a mixture of diester(s) and cyclohexane derivative(s) |
| DD208167A5 (de) * | 1980-12-23 | 1984-03-28 | Hoffmann La Roche | Decaline |
| US4577930A (en) * | 1982-05-24 | 1986-03-25 | International Business Machines Corporation | Weak boundary storage liquid crystal display devices with bias voltage |
| US4550981A (en) * | 1982-09-30 | 1985-11-05 | Hoffmann-La Roche Inc. | Liquid crystalline esters and mixtures |
| US4680137A (en) * | 1985-06-10 | 1987-07-14 | Chisso Corporation | Liquid crystal ester compound |
| JPH01131693A (ja) * | 1987-11-17 | 1989-05-24 | Ace Premium:Kk | 玩具用眼球装置 |
| JPH0632154Y2 (ja) * | 1988-02-29 | 1994-08-24 | 株式会社タカラ | 人形の活眼装置 |
| EP0341922B1 (en) * | 1988-05-12 | 1994-07-27 | Mitsui Petrochemical Industries, Ltd. | Naphthalene compound and liquid crystal composition containing the same |
| JPH0430590U (enrdf_load_stackoverflow) * | 1990-07-03 | 1992-03-11 | ||
| ATE118523T1 (de) * | 1990-07-19 | 1995-03-15 | Mitsui Petrochemical Ind | Flüssigkristall-racematmischung, flüssigkristallzusammensetzung und flüssigkristallelement, verfahren zur herstellung und verwendung. |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3915883A (en) * | 1972-04-26 | 1975-10-28 | Eastman Kodak Co | Liquid crystalline compounds and compositions |
| GB1433130A (en) * | 1972-11-09 | 1976-04-22 | Secr Defence | Substituted biphenyl and polyphenyl compounds and liquid crystal materials and devices containing them |
| US3971824A (en) * | 1973-08-15 | 1976-07-27 | Eastman Kodak Company | P-Benzoyloxybenzoate |
| US4009934A (en) * | 1974-01-11 | 1977-03-01 | Eastman Kodak Company | Electro-optic display devices and methods |
| US3925237A (en) * | 1974-06-28 | 1975-12-09 | Rca Corp | Novel liquid crystal electro-optic devices |
| DE2538865A1 (de) * | 1974-09-03 | 1976-03-11 | Beckman Instruments Inc | Nematische fluessigkristallmassen |
-
1976
- 1976-08-13 GB GB33861/76A patent/GB1587819A/en not_active Expired
-
1977
- 1977-08-04 US US05/821,919 patent/US4119558A/en not_active Expired - Lifetime
- 1977-08-05 CA CA000284208A patent/CA1120490A/en not_active Expired
- 1977-08-05 ZA ZA00774755A patent/ZA774755B/xx unknown
- 1977-08-10 AU AU27774/77A patent/AU517766B2/en not_active Expired
- 1977-08-11 SE SE7709092A patent/SE7709092L/ not_active Application Discontinuation
- 1977-08-12 DK DK359877A patent/DK359877A/da not_active Application Discontinuation
- 1977-08-12 FR FR7724975A patent/FR2361457A1/fr active Granted
- 1977-08-12 JP JP52097432A patent/JPS5929184B2/ja not_active Expired
- 1977-08-12 NL NL7708941A patent/NL7708941A/xx not_active Application Discontinuation
- 1977-08-12 DE DE2736502A patent/DE2736502C2/de not_active Expired
- 1977-08-12 BE BE180170A patent/BE857785A/xx not_active IP Right Cessation
- 1977-08-15 CH CH996377A patent/CH636636A5/de not_active IP Right Cessation
- 1977-08-16 AT AT592677A patent/AT352105B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DK359877A (da) | 1978-02-14 |
| US4119558A (en) | 1978-10-10 |
| CA1120490A (en) | 1982-03-23 |
| ATA592677A (de) | 1979-02-15 |
| SE7709092L (sv) | 1978-02-14 |
| GB1587819A (en) | 1981-04-08 |
| FR2361457B1 (enrdf_load_stackoverflow) | 1981-01-02 |
| NL7708941A (nl) | 1978-02-15 |
| ZA774755B (en) | 1978-06-28 |
| BE857785A (fr) | 1977-12-01 |
| AU517766B2 (en) | 1981-08-27 |
| CH636636A5 (de) | 1983-06-15 |
| JPS5929184B2 (ja) | 1984-07-18 |
| AT352105B (de) | 1979-09-10 |
| AU2777477A (en) | 1979-02-15 |
| FR2361457A1 (fr) | 1978-03-10 |
| JPS5322884A (en) | 1978-03-02 |
| DE2736502A1 (de) | 1978-02-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |